{"id":6674,"date":"2026-08-12T17:37:30","date_gmt":"2026-08-12T17:37:30","guid":{"rendered":"https:\/\/nextcitydigest.com\/?p=6674"},"modified":"2026-08-12T17:37:30","modified_gmt":"2026-08-12T17:37:30","slug":"expecting-his-first-child-jon-hamm-joins-long-list-of-old-hollywood-dads","status":"publish","type":"post","link":"https:\/\/nextcitydigest.com\/?p=6674","title":{"rendered":"Expecting his first child, Jon Hamm joins long list of ‘old’ Hollywood dads"},"content":{"rendered":"
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It\u2019s easy to see how Jon Hamm is following a similar path as Don Draper, the handsome but elusive 1960s advertising executive he played on \u201cMan Men.\u201d After splitting from his longtime female partner, who\u2019s more or less his contemporary, Hamm, like Draper, has taken up with a much younger woman.<\/p>\n

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In Hamm\u2019s case, he\u2019s also now starting a family with his new partner, actor Anna Osceola, making him a first-time father at 55.<\/p>\n

While Draper got kicked out of the house by Betty, the mother of his three children, and married his pretty young secretary, Hamm ended an 18-year relationship with actor, screenwriter and occasional collaborator Jennifer Westfeldt in 2015. Westfeldt is a year older than Hamm, while Osceola is 17 years his junior. She also had a small role in \u201cMad Men.\u201d Hamm and Osceola married in 2023 \u2014 in a cliffside ceremony in Big Sur overlooking the Pacific Ocean.<\/p>\n

Before it was reported this week that the \u201cYour Friends & Neighbors\u201d star and Osceola were expecting a baby, he told The Hollywood Reporter that he was looking forward to finally having children, as People reported. \u201cIt\u2019s not lost on me that I\u2019m (in my 50s),\u201d he admitted. \u201cI will be the old dad, but so it goes. It could be a good thing. We\u2019ll see.\u201d<\/p>\n

Of course, Hamm isn\u2019t the first male celebrity to be an \u201cold dad.\u201d It\u2019s a longstanding Hollywood tradition \u2014 a cliche even. There\u2019s a long list of famous male celebrities who have welcomed babies with much-younger wives and girlfriends when they are in their 50s, 60s, 70s and even their 80s: Robert De Niro, Al Pacino, Bruce Willis, Mick Jagger, Alec Baldwin, Mel Gibson, Eddie Murphy and Richard Gere.<\/p>\n

Hamm also belongs in a sub-set of this cliche: Male celebrities who become first-time fathers when they are 50 or older.<\/p>\n

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George Clooney, once one of Hollywood\u2019s most famous bachelors, became a first-time father at age 56 in 2017 when his wife Amal Clooney, then 39, gave birth to twins. After Justin Theroux split from 57-year-old Jennifer Aniston in 2018, the now-55-year-old actor married 32-year-old actor Nicole Brydon Bloom last year. Theroux became a first-time father to a son in April, with the couple announcing on Instagram: \u201cHe\u2019s here. We are so in love.\u201d<\/p>\n

Then there is Steve Martin, now 80, who became a first-time father in 2012 at age 67 with his writer wife, Anne Stringfield. Hugh Grant also became a first-time father in 2012 when he was 51, and has since gone on to have five children with two different women.<\/p>\n

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Perhaps the most famous case of a male celebrity who got started late in fatherhood, after making a name for himself as a bachelor who enjoyed the company of a variety of women, is Warren Beatty. Now 89, Beatty dated Natalie Wood, Joan Collins, Leslie Caron, Carly Simon, Julie Christie, Diane Keaton and Madonna, to name just a few. In 1992, at age 55, the star of \u201cBonnie and Clyde,\u201d \u201cShampoo\u201d and \u201cReds\u201d married actor Annette Bening, then 34. Together, they quickly had four children.<\/p>\n

As for Hamm, he opened up in a 2022 interview with Howard Stern about finally being ready to settle down, marry and have children after he met Osceola, as People reported.<\/p>\n

\u201cThis is another place in my life that I feel very settled and comfortable,\u201d Hamm said on Stern\u2019s SiriusXM show. \u201cI\u2019m in a relationship right now and it\u2019s comfortable.\u201d He also said the relationship is \u201cmore meaningful and (has) opened up the possibility of things like being married, having kids, defining a new version of happiness, life, wellness.\u201d<\/p>\n

Read more \u2018Independent boutique grocery store\u2019 coming to downtown San Jose<\/a><\/p>\n<\/div>\n<\/div>\n","protected":false},"excerpt":{"rendered":"

It’s a longstanding Hollywood tradition — a cliche even — of male celebrities getting together with much younger women and having children in their 50s, 60s, 70s and even their 80s.<\/p>\n","protected":false},"author":1,"featured_media":6673,"comment_status":"open","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[4],"tags":[],"class_list":["post-6674","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-things-to-do"],"yoast_head":"\nExpecting his first child, Jon Hamm joins long list of ‘old’ Hollywood dads - Next City Digest<\/title>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/nextcitydigest.com\/?p=6674\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Expecting his first child, Jon Hamm joins long list of ‘old’ Hollywood dads - 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